


Dean & Co.

by toowincesttolive



Category: Supernatural
Genre: Anal Fingering, Anal Sex, BDSM, Bondage, D/s, Destiel - Freeform, Dom Sam, Dom/sub, Gangbang, M/M, Multi, Oral Sex, Plot What Plot/Porn Without Plot, Rough Sex, Sub Dean, Wincest - Freeform, ballgag, gagged and bound
Language: English
Status: Completed
Published: 2015-10-14
Updated: 2015-11-26
Packaged: 2018-04-26 07:50:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,302
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4996579
Author URL: https://archiveofourown.org/users/toowincesttolive/pseuds/toowincesttolive
Summary: <blockquote class="userstuff"><p>I tried to keep everything as healthy and safe as possible, but this story is still fictional and is not 100% okay BDSM wise. Basically just please don't use this as any kind of guide to BDSM and please don't yell at me if I got something wrong (although polite, constructive criticism is always welcome)</p></blockquote>





	1. Dean & Co. Prequel

Sam’s eyes softened and he sat on the bed, pulling Dean next to him, petting his hair gently. “What is your safe word?” He asked.

“Impala.”

“Good, Dean. What do you do if you cannot speak?”

“Snap twice.”

“Good. I want you to do that right now.”

Two snaps.

“Good boy. Do not do anything you do not want to, okay? I love you,” Sam kissed him without any heat, just as a reiteration of what he just said.

He pulled back with the mischievous look working into his eyes. “Are you ready to get to the fun part?”

Dean nodded, a hint of nervousness creeping into the back of his mind.

“I’ve got a surprise for you tonight, Dean.,” Sam’s cocky tone sent shivers down his spine. Whatever this was, Sam had been planning it for a while.

Dean swallowed hard, but didn’t say anything. He looked at Sam and waited for further instruction.

“Strip,” Sam demanded, staring him down. It made Dean feel self-conscious, though he knew he was safe with Sam. Dean unbuttoned his shirt carefully. Then, he removed his t-shirt and jeans. He looked up and met Sam’s unwavering eyes uneasily. He swallowed a gulp of air and pushed down his boxers as well. He folded each item delicately and placed them in their designated spots, still feeling Sam’s eyes on him the entire time.

“We’re going to the playroom, Dean. I want your eyes on the ground behind me until I have shut the door. You know I will know if your eyes leave the ground, and you will be punished.”

Dean followed Sam’s words to a T down the hallway and into the “playroom” which was originally another dungeon. Sam decided he liked it better with a different use. The only sound was Dean’s breathing and the slap of his bare feet on the hard cement floors.

Sam turned to watch Dean follow him into the playroom. He watched him shuffle in with his eyes still cast down, then waited. He could see Dean fighting the urge to look around fidget. Finally, Sam stepped forward and shut the door.

Dean sighed, and tentatively looked up around the room. Sam walked to the chest at the end of the room and lifted the top. He pulled out a few items, but blocked them from Dean’s view.

“First things first, you’ll need this,” Sam pulled out the red ball gag, Dean’s favorite. “And I’m going to tie you to the bench. They’ll probably let you go at some point, but I want them to see what you are and how you belong to begin, first.”

Dean trembled at Sam’s words. He didn’t know who they were, but he had an idea. He was already rock hard, and Sam had barely given a glance at his cock. He complied easily as Sam spread his legs and tied down his arms.

Sam let Dean test his bonds when he was finished and took a satisfied breath when they held.

“One last toy,” Sam said. He took out the cherry red cockring and showed it to Dean. Dean whined softly, knowing it would be a long night.

“I’m going to open you up first,” Sam said, popping the cap on a bottle of lube. He coated a finger and prodded Dean’s ass gently with one finger. He pushed it in slowly, twisting and working him open. Dean’s breaths were slightly harsher as he continued. Sam added another finger with his first, twisting and scissoring Dean’s ass, enjoying the punched out breathes he pulled from his brother.

“You’re doing so good, Dean,” He said. He added a third finger, then a fourth, pushing and stretching Dean so he would be ready.

Once Sam was satisfied with his progress, he left the lube on a table near Dean’s ass and stepped back to admire his work. He was still fully clothed and regretting his choice to wear jeans this morning as his erection pressed against his zipper.

Sam stood next to Dean and called, “Alright boys, come on out.”

Dean strained to look over his shoulder as Benny, Castiel, and Cole entered through the playroom door.

Their eyes raked over Dean’s body, and it made Sam immediately defensive. “First things first, gentlemen. I know you all care about Dean and would never intentionally hurt him. However, if you do hurt him in any way that he does consent to, I do not need to tell you that I hunt you down and kill you, human, angel, or vampire.” Sam met the eyes of each of them as he said this.

“You will all also respect Dean’s safe words,” Sam said. “Dean, I want you to give your nonverbal safe word now.”

Two snaps.

Sam removed the gag. “Your verbal safe word, please.”

“Impala.” Sam replaced the gag.

“Understood?” Each of the three men nodded solemnly.

Sam took a stride away from Dean to the corner of the room.

“Enjoy.”


	2. Dean & Co Part 2

**Notes for the Chapter:**

> I tried to keep everything as healthy and safe as possible, but this story is still fictional and is not 100% okay BDSM wise. Basically just please don't use this as any kind of guide to BDSM and please don't yell at me if I got something wrong (although polite, constructive criticism is always welcome)

Everyone hesitated, all of them wanting Dean, but none of them willing to make the first move.

Benny was the first to break. He took a step forward and put one hand on Dean’s ass, whistling as he walked around the bench, dragging his hand across Dean’s body.

“I’ve wanted to do this for a long time,” He said, the same drawl coloring his tone.

A shiver ran up Dean’s spine, starting from the hot touch of Benny’s hand.

Benny met the eyes of Cole. “I know you want him, too. Can’t let me have all the fun.”

Dean, for his part, was still hard and drooling and starting to get a little chilly. He and Sam had discussed this in detail, though not with the other three. He knew Sam had given some other, undoubtedly more detailed words before bringing them in. Dean was beginning to wonder if Sam asked them to wait until he was shivering.

The thought didn’t get too far from Dean’s mind before Cas was at Dean’s ass, tracing his open hole with a lubed finger, occasionally dipping in. Dean moaned at the contact. Cas met the eyes of the other two with a hint of a smirk. As bold as Benny might have thought he was, Cas would be the first one to fuck Dean tonight. He was sure as hell proud of himself for it, too.

Cas quickly unzipped his pants and pushed the waistband of his boxers down, freeing only his cock. He pumped a healthy amount of lube into his hand, covered his cock, and guided it into Dean’s ass, loving the heat and Dean’s squirms and moans of pleasure. Cas pulled out to the head and thrust back in, working up to a harsh pace.

Dean’s moans quieted to harsh breaths. That and the slap of skin on skin were the only sounds in the room for a few seconds, then everyone seemed to want in on it at once.

Cole moved from his spot on the wall to Dean’s face, using one hand to unbutton his jeans and the other to reach the back of Dean’s neck to take out the ball gag. He wasted no time to push his jeans and underwear to his knees, freeing an impressive dick.

Cole ran a thumb around Dean’s lips. “You’ve always had those pretty, cocksucking lips, Dean-o. Always wanted to use them like this.”

Dean licked his lips and opened his mouth for Cole to use. He took the head into his mouth, swirling his tongue around the tip. Cole pushed in further, and Dean took every inch, deepthroating his cock until it hit the back of his throat. Cole stayed there for a moment, relishing the warmth of Dean’s mouth and his pretty green eyes looking up at him.

Then, he pulled out of Dean’s mouth slightly and pushed back in. He wanted to take his time using and abusing Dean’s mouth before he shot his load all over Dean’s pretty, freckled face.

Benny found his hand pressing against his jeans at the sight. Cas and Cole spitroasting Dean on their cocks was enough to make anyone come just watching them. Their eyes met as they kept going and developed a rhythm. Cas’ thrusts into Dean pushed Dean’s mouth further onto Cole’s cock. Cole made sure to thrust at the same time so Dean would be completely stuffed from both ends.

But Benny was currently interested in Dean’s straining, untouched cock. He didn’t touch the cock ring, but he ran a finger on the underside of Dean’s cock, watched it jump from his fingers. He wrapped his hand around it, and jerked Dean slowly, causing near-screams around Cole’s cock in his mouth.

Cas felt heat starting to build in his stomach and pulled out of Dean’s ass. He didn’t want to come, yet, and not in Dean’s ass. Cas wanted to see Dean’s face painted with his come like a whore.

“Hey, Benny,” Cas called, “You want a turn?”

“Oh, hell yes,” Benny replied eagerly, abandoning Dean’s cock. He wasn’t nearly as gentle as Cas had been. He took just enough time to lube up his dick and pushed in, fucking Dean roughly, grabbing his hips hard enough to leave bruises and forcing his mouth further onto Cole’s cock.

Cole pulled out of Dean’s mouth as he got nearer to his orgasm and jacked himself off into Dean’s wide, open mouth and on his cheeks and eyelashes. Dean swallowed what landed into his mouth and licked his lips, but he could feel the rest drying on his cheeks and eyelashes. He didn’t have a chance to speak before Cas was in front of him, forcing his cock down Dean’s throat.

Cas and Benny fucked Dean from both ends for a while. Cole sat down in the corner of the room to watch them, quickly getting hard again.

Sam watched from the corners of the room. the sight was incredibly hot, but Sam left his neglected dick in his jeans, watching his brother and the three men like a hawk, ready to put an end to everything at the slightest sign that Dean was not okay.

Cas came first into Dean’s mouth and pulled out to shoot the rest of his load onto Dean’s face over Cole’s dried come. Benny followed, filling up Dean’s ass with his come and pulling out.

For a moment, nothing happened. Benny, Cas, and Cole were breathing hard following their orgasms. Dean bit back whines in the back of his throat, now left empty and still desperate to come. Sam still watched from the shadowed corner of the room, palming his cock every now and then when he just couldn't help it. This was about Dean; he was just there to keep everyone in line.

Cas, being an angel, had a two second recovery and was ready for round two before the others. Cole was hard again not long after. But, this time they decided to get the full range of things that Dean could do.

They untied him from the bench and pushed him onto the the floor gingerly. As soon as he was situated, Cas gave him a questioning look. Dean gave him a thumbs up to show he was still fine, and Cas pushed him to his hands and knees, more forcefully this time.

Cole went back to Dean’s mouth and wasted no time pushing in and grabbing a handful of Dean’s hair to fuck him onto his cock. “Fuck, you look so hot,” he groaned, “So pretty with a mouthful of cock.”

Dean moaned, but he was starting to feel dehydrated. He didn’t think to drink enough water before this. His mouth felt dry, and he was starting to feel less than great.

Dean snapped twice, but Sam was on top of Dean and sent Cole and Cas flying across the room before Dean has actually snapped twice. A half-thought protest was obvious on Cole’s face, but he didn’t even dare to complete the thought in his mind. Cas and Cole didn’t move from their corners, though. Benny stayed put. There was an air of respect and fear in the room while Sam was in control.

Once Sam was sure the other three were in their places, he turned his full attention to Dean. He ran his hands over Dean’s body, looking for any scrapes or sensitivity. They were there, of course, but Dean just mouthed “water” towards Sam. Sam had three water bottles in his hand and pressed one into Dean's faster than should be humanly possible. Sam already had several water bottles and light snacks for Dean in case something like this happened. He was already hitting himself internally for not getting Dean more water beforehand. Next time, if Dean ever wanted this again, Sam would be sure to get plenty of water into his system before anything fun happened.

Sam made Dean down the whole bottle before he let him speak at all.

“Are you okay? Do you want to stop? It’s okay if you aren’t comfortable, Dean.” Sam questioned.

Dean finished the bottle with a sigh. “I’m okay, Sammy.” Dean’s voice was a little strained, but he was otherwise fine. “Let’s keep this going,” he grinned.

Sam took a deep breath and helped Dean back to his knees. He gave another harsh look to Benny, Cas, and Cole. “Okay,” he said. “You can continue.” He moved back to his corner of the room to watch again.

The little break hadn’t taken longer than three minutes, and Cole was back at Dean’s mouth within seconds. He got right back to where he was with his hand fisted in Dean’s hair. The tip of Cas’ cock nudged Dean’s hole again. He was still open, and Benny’s come was slowly leaking out of Dean’s hole, but Cas kept it plugged with his cock and worked up to speed again.

Benny finally came off the bench and joined Cas at Dean’s ass.

“Do you think he could take two?” Benny asked Cas, loud enough for Dean and Sam to hear. He wanted this, but he wouldn’t do a thing either of the brothers were uncomfortable with. He didn’t hear a protest, but he walked around to see Dean’s face to be sure.

“Take a break, would ya?” He glared at Cole.

Cole let go of Dean and pulled out of his mouth so Dean could nod his head in response to Benny’s question.

Cole resumed fucking Dean mouth again while Benny started opening Dean up further while Cas continued to fuck his ass.

“Gonna take this nice and slow,” Benny said softly. He used the lube Sam had left out and coated his finger thickly before working it in Dean beside Cas’ cock. It was tight fit, but Dean's muffled moans made it better. He got one finger in to the knuckle and bent and moved it significantly. So far tonight, no one had had much focus on Dean’s prostate while fucking him. They’d hit it a few times, but they hadn’t purposefully avoided or targeted it. Now, Benny was searching for it. He wanted Dean sobbing with need before he would take that red cock ring off and let him come.

Benny worked in a second finger, stretching and pulling around Cas’ cock. With the other hand, Benny place feather light touches along Dean’s neglected cock.

Dean was squirming and moaning more than he had all night while Benny worked more fingers into his ass next Cas’ cock. Cole was also ever-present in his mouth. Fucking into his mouth mouth relentlessly with no sign of slowing or reaching his second orgasm yet.

Benny was finally satisfied with four fingers moving fairly smoothly in and out of Dean’s ass. He covered his cock in an extra coating of lube and lined up next to Cas at Dean hole.

Cas didn’t move while Benny pressed in, just letting Dean feel so filled from both ends, being overwhelmed by the pleasure and pain.

Dean sobbed around Cole’s cock, desperate for release, but knowing he had a long way to go to get there.

Benny and Cas set a slow, increasing pace, fucking rhythmically with each other and Dean.

They worked up to a frantic pace, one of them always pressing against Dean’s prostate. As they got closer to their orgasms, Cole approached his. All three of them fucked harder and faster.

Dean eyes rolled back in his head, This was almost too much for him. His holes stuffed up so full and pretty, pressing all of his buttons as once.

Benny cupped Dean’s balls in one hand while still keeping a firm grasp on his hip. His fingers were in the same tender places they had been earlier, and the added pain just added more to Dean’s stimulation.

Benny felt a tightening in his stomach and moved his hand from Dean’s balls to unlock the cock ring. He fucked even harder, though he wasn’t sure that was possible, and finally pushed over the top at the same time as Cas and Cole into Dean’s mouth and ass.

The feeling was so overwhelming and sudden, it pushed Dean completely over the top and he came shooting up onto his chest and all over the floor. And he kept coming, and the men fucking him kept fucking as they rode out their orgasms. It was possibly the most intense orgasm of Dean's life. His vision went white at the edges, and he knew he was close to passing out.

Cole pulled out of Dean’s mouth first, then Benny and Cas from his ass. He felt empty, and almost whined, but he knew he had reached his limits. He was so tired, he just wanted to drift off to sleep.

Sam caught the attention of the three men, and they knew their time was up. He went to Dean with a warm, moist towel, collecting the sweat and come piled on his face and neck. He tried to clean his stomach a little, and scooped up the come leaking out of his hole.

Sam covered Dean with a thin blanket for comfort rather than warmth and ran a hand through his hair, petting him gently.

“You were so good, Dean. So good. WIll you be okay for a minute while I let our… guests… out?”

Dean nodded and Sam gently laid his head against a pillow.

Sam got up and tossed a water bottle to Cole. The other two didn’t really need to stay hydrated, since they weren’t really human.

Sam allowed them to pick up their discarded clothes and led them to one of the many living rooms they had. It was where they’d been waiting before, so they knew their way out. Sam didn’t really say anything to them because there wasn’t much to say.

Sam padded quickly back to the room where Dean was lying. Sam sat him up and made him drink about half a bottle of water before they did anything else.

Sam pressed his lips against Dean’s forehead, repeating words of praise to Dean.

Before Sam could get him on his feet, Dean drifted off to sleep. Sam mostly carried him to the nearest bedroom, and got him on the bed. He laid down beside him and rubbed his back as he slept. When he woke up again, they would move upstairs to Dean’s room. Right now, Sam didn’t think either of them had the willpower to make it all the way up the stairs and down the hall.

Sam wrapped his arms around Dean and pulled him to his chest with the few of the covers over both of them. He pressed his nose into Dean’s neck.

“I love you,” He whispered to Dean as he fell into a light sleep at Dean’s back.

**Notes for the Chapter:**

> This is the end of Dean's sexcapade. Thank you for reading it, and if you liked it PLEASE comment or leave kudos!!

**Author's Note:**

> This is the very beginning to hopefully what will be a two part story. If you like what is here so far, PLEASE leave kudos, comment, or subscribe!!


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